I can imagine a situation where the employees of the condotel management company provide services for all the units in the building and no one individual spends more time on your unit than you do.  

An employee of mine was looking at renting a house in the area that I lived in, and I thought "Wow, what a perfect opportunity to rent my house out and buy a multi-family property".

However, we aren’t W2 employees, all that income is from 1099 independent contractor work, which of course will limit what financing we can qualify for.

I would have never known otherwise, just a quick phone call (make sure you talk to a knowledgeable/caring employee as govt employees sometimes are not).

This forum has been a great resource for learning thus far, thank you everyone for contributing.My spouse and I are W2 employees and have a few investment properties but all of them are LTR.

If you expect to have a more dynamic need - say you'll be investing nation wide and will need to address State and Local Tax issues in a number of different jurisdictions, or you'll be buying a property in the Caribbean, or you want tax advice on your estate/trust/gift planning, or now you are hiring employees and you want to ensure you are getting help when it comes to tax considerations of your employee benefit plans, or whatever avenue you go - maybe a Regional firm or one specialized in real estate all over will be your best fit over the more mom and pop practitioner.I always disagree with needing to work with an accountant that invests. 

At the time, I had several rentals, a side software business, and then bought a business with 8 employees.

Would it make sense to start your own PM company for this purpose and have spouse as sole employee who receives compensation from the small rental portfolio? 

I know a commercial tenant (colleague) who is paying to rent an office space big enough for 40 employees, but only 5 people are willing to go to the office, so it's a ghost town, obviously they will not be renewing.

Employers looking for temporary housing for employees will lease them.